Chlorosulfonic acid → N-methanesulfonyl-5-chlorosulfonyl-2-aminobenzimidazole

HRID 1166462

Reaktionsgleichung

Reaktionsgleichung von HRID 1166462
[Cl:1][S:2]([OH:5])(=O)=[O:3].[CH3:6][S:7]([N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]=[C:11]1[NH2:19])(=[O:9])=[O:8].C(=O)(O)[O-].[Na+]>O>[CH3:6][S:7]([N:10]1[C:14]2[CH:15]=[CH:16][C:17]([S:2]([Cl:1])(=[O:5])=[O:3])=[CH:18][C:13]=2[N:12]=[C:11]1[NH2:19])(=[O:8])=[O:9]

Komponenten

5

Edukt 3

HCID 24638Chlorosulfonic acidHCID 516892Sodium BicarbonateHCID 229970451-(Methylsulfonyl)-1H-Benzimidazol-2-Amine

Produkt 1

HCID 22997216N-methanesulfonyl-5-chlorosulfonyl-2-aminobenzimidazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To 9.5 mL (20 eq., 142 mmol) of well stirred chlorosulfonic acid at ˜25° C. was added N-methanesulfonyl-2-aminobenzimidazole (1.5 g, 7.1 mmol) in small portions over 1C minutes with slight exotherming. The solution was stirred at ˜25° C. for 3.5 hours, then was added dropwise to a well stirred mixture of ice and water. The aqueous solution was slowly basified to pH ˜7.5 with solid sodium bicarbonate and extracted with EtOAc. A precipitate formed in the organic phase which was filtered off and was washed with H20 and dried on the filter to yield 1.23 g of N-methanesulfonyl-5-chlorosulfonyl-2-aminobenzimidazole. HPLC, single peak, ret. time=7.61 min. MS: Obs. M +H@ 310.0 amu.

Aufarbeitung

  1. additionwas added dropwise to a well
  2. stirringstirred
  3. extractionextracted with EtOAc
  4. customA precipitate formed in the organic phase which
  5. filtrationwas filtered off
  6. washwas washed with H20
  7. customdried on the
  8. filtrationfilter

Quellen und Nachweise

ORD-Eintrag
ord-4e5339decb32429eadc0cf684119054e
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06613743B2

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